Citation: Yong Xue-Feng, Huang Jian-Qiang, Ho Chun-Yu. Applications of (NHC)Ni(Ⅱ) Catalyzed [3+2] Hydroalkenylation-Rearrangement Cascades[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3327-3337. doi: 10.6023/cjoc202005050 shu

Applications of (NHC)Ni(Ⅱ) Catalyzed [3+2] Hydroalkenylation-Rearrangement Cascades

Yong Xue-Feng ^a,b,c,d,† ,
Huang Jian-Qiang ^b,c,d,†,, ,
Ho Chun-Yu ^b,c,d,,

a.
School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001
b.
Shenzhen Grubbs Institute, Shenzhen, Guangdong 518055
c.
Guangdong Provincial Key Laboratory of Catalysis, Shenzhen, Guangdong 518055
d.
Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055

Corresponding author: Huang Jian-Qiang, huangjq3@sustech.edu.cn Ho Chun-Yu, jasonhcy@sustech.edu.cn
Received Date: 19 May 2020
Revised Date: 2 July 2020
Available Online: 15 July 2020
Fund Project: the Guangdong Basic and Applied Basic Research Foundation-Youth Project 2019A1515110001Project supported by the Guangdong Basic and Applied Basic Research Foundation-Youth Project (No. 2019A1515110001)

Figures(12)

Synthetic applications of the recently developed (NHC)Ni(Ⅱ) catalyzed[3+2] hydroalkenylation-rearrangement cascade (HARC) were investigated. The foundations of these highly substituted cyclopentadienes and methylene cyclopentanes formation were compared with typical cross-hydroalkenylation of alkenes and dienes. The desired cyclization products were examined as key starting materials for a range of olefin functionalization methodology, including Diels-Alder, epoxidation, ozonolysis, halogenation-rearrangement and fluorohydroxylation. The results showed that several very interesting carbon skeletons can be obtained easily with high diastereoselectivity in one step or in cascade.
- strained alkene,
- [3+2] cycloaddition,
- N-heterocycle carbenes,
- Ni catalysis,
- cross-hydroalkenylation
1. [1]
  (a) Romano, C.; Mazet, C. J. Am. Chem. Soc. 2018, 140, 4743.
  (b) Chen, J.; Guo, J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075.
2. [2]
  Wilke, G. Angew. Chem. Int. Ed. 1988, 27, 185. doi: 10.1002/anie.198801851
3. [3]
  Bogdanović, B.; Spliethoff, B.; Wilke, G. Angew. Chem. Int. Ed. 1980, 19, 622. doi: 10.1002/anie.198006221
4. [4]
  (a) Rieu, J.-P.; Boucherle, A.; Cousse, H.; Mouzin, G. Tetrahedron 1986, 42, 4095.
  (b) Sonawane, H. R.; Bellur, N. S.; Ahuja, J. R.; Kulkarni, D. G. Tetrahedron: Asymmetry 1992, 3, 163.
5. [5]
  Ziegler, K.; Cellert, H. G.; Holzkamp, E.; Wilke, G. Brennst. Chem. 1954, 35, 321.
6. [6]
  (a) Ziegler, K.; Holzkamp, E.; Breil, H.; Martin, H. Angew. Chem. Int. Ed. 1955, 67, 426.
  (b) Wilke, G. Angew. Chem. Int. Ed. 1957, 69, 397.
  (c) Wilke, G. Angew. Chem. Int. Ed. 1960, 72, 581.
  (d) Wilke, G.; Bogdanov. B. Angew. Chem. Int. Ed. 1961, 73, 756.
  (e) Wilke, G.; Kroner, M.; Bogdanov, B Angew. Chem. Int. Ed. 1961, 73, 755.
  (f) Wilke, G.; Herrmann, G. Angew. Chem. Int. Ed. 1966, 5, 581.
  (g) Bogdanov. B; Wilke, G. Brennst.-Chem. 1968, 49, 323.
7. [7]
  RajanBabu, T. V. Chem. Rev. 2003, 103, 2845. doi: 10.1021/cr020040g
8. [8]
  Kawata, N.; Maruya, K.-i.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 3217. doi: 10.1246/bcsj.44.3217
9. [9]
  (a) Ceder, R.; Muller, G.; Ordinas, J. I. J. Mol. Catal. 1994, 92, 127.
  (b) Monteiro, A. L.; Seferin, M.; Dupont, J.; de Souza, R. F. Tetrahedron Lett. 1996, 37, 1157.
  (c) Wegner, A.; Leitner, W. Chem. Commun. 1999, 1583.
  (d) Nomura, N.; Jin, J.; Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 459.
10. [10]
  (a) Shi, W.-J.; Zhang, Q.; Xie, J.-H.; Zhu, S.-F.; Hou, G.-H.; Zhou, Q.-L. J. Am. Chem. Soc. 2006, 128, 2780.
  (b) Zhang, Q.; Zhu, S.-F.; Qiao, X.-C.; Wang, L.-X.; Zhou, Q.-L. Adv. Synth. Catal. 2008, 350, 1507.
  (c) Zhang, Q.; Zhu, S.-F.; Cai, Y.; Wang, L.-X.; Zhou, Q.-L. Sci. China Chem. 2010, 53, 1899.
11. [11]
  Li, K.; Li, M.-L.; Zhang, Q.; Zhu, S.-F.; Zhou, Q.-L. J. Am. Chem. Soc. 2018, 140, 7458. doi: 10.1021/jacs.8b04703
12. [12]
  Clement, N. D.; Cavell, K. J. Angew. Chem. Int. Ed. 2004, 43, 3845. doi: 10.1002/anie.200454166
13. [13]
  Ho, C.-Y.; He, L. Angew. Chem. Int. Ed. 2010, 49, 9182. doi: 10.1002/anie.201001849
14. [14]
  Ho, C.-Y.; Chan, C.-W.; He, L. Angew. Chem. Int. Ed. 2015, 54, 4512. doi: 10.1002/anie.201411882
15. [15]
  Ho, C.-Y.; He, L. Chem. Commun. 2012, 48, 1481. doi: 10.1039/C1CC14593B
16. [16]
  (a) Lian, X.; Chen, W.; Dang, L.; Li, Y.; Ho, C.-Y. Angew. Chem. Int. Ed. 2017, 56, 9048.
  (b) Chen, Y.; Dang, L.; Ho, C.-Y. Nat. Commun. 2020, 11, 2269.
17. [17]
  Chen, W.; Li, Y.; Chen, Y.; Ho, C.-Y. Angew. Chem. Int. Ed. 2018, 57, 2677. doi: 10.1002/anie.201712693
18. [18]
  Ho, C.-Y.; He, L. J. Org. Chem. 2014, 79, 11873. doi: 10.1021/jo5008477
19. [19]
  Huang, J.-Q.; Ho, C.-Y. Angew. Chem. Int. Ed. 2019, 58, 5702. doi: 10.1002/anie.201901255
20. [20]
  Huang, J.-Q.; Ho, C.-Y. Angew. Chem. Int. Ed. 2020, 59, 5288. doi: 10.1002/anie.201914542
21. [21]
  Kumareswaran, R.; Nandi, M.; RajanBabu, T. V. Org. Lett. 2003, 5, 4345. doi: 10.1021/ol0356284
22. [22]
  Wong, H. N. C.; Hon, M. Y.; Tse, C. W.; Yip, Y. C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. doi: 10.1021/cr00091a005
23. [23]
  (a) Zhang, G.-P.; Huang, S.; Jiang, Y.-J.; Liu, X.-Y.; Ding, C.-H.; Wei, Y.; Hou, X.-L. Chem. Commun. 2019, 55, 6449.
  (b) Huang, J.-Q.; Liu, W.; Zheng, B.-H.; Liu, X. Y.; Yang, Z.; Ding, C.-H.; Li, H.; Peng, Q.; Hou, X.-L. ACS Catal. 2018, 8, 1964.
  (c) Huang, J.-Q.; Zhao, J.-F.; Yang, Z.; Ding, C.-H.; Hou, X.-L.; Peng, X.-S.; Wong, H. N. C. Asian J. Org. Chem. 2017, 6, 1769.
  (d) Huang, J.-Q.; Ding, C.-H.; Hou, X.-L. J. Org. Chem. 2014, 79, 12010.
  (e) Liu, W.; Chen, D.; Zhu, X.-Z.; Wan, X.-L.; Hou, X.-L. J. Am. Chem. Soc. 2009, 131, 8734.
24. [24]
  (a) Fumagalli, G.; Stanton, S.; Bower, J. F. Chem. Rev. 2017, 117, 9404.
  (b) Simaan, M.; Marek, I. Angew. Chem. Int. Ed. 2018, 57, 1543.
  (c) Wang, X.-B.; Zheng, Z.-J.; Xie, J.-L.; Gu, X.-W.; Mu, Q.-C.; Yin, G.-W.; Ye, F.; Xu, Z.; Xu, L.-W. Angew. Chem. Int. Ed. 2020, 59, 790.
  (d) Shi, M.; Shao, L.-X.; Lu, J.-M.; Wei, Y.; Mizuno, K.; Maeda, H. Chem. Rev. 2010, 110, 5883.
  (e) Zhao, Z.-Y.; Nie, Y.-X.; Tang, R.-H.; Yin, G.-W.; Cao, J.; Xu, Z.; Cui, Y.-M.; Zheng, Z.-J.; Xu, L.-W. ACS catal. 2019, 9, 9110.
25. [25]
26. [26]
27. [27]
28. [28]
  (a) Funami, H.; Kusama, H.; Iwasawa, N. Angew. Chem. Int. Ed. 2007, 46, 909.
  (b) Lee, J. H.; Toste, F. D. Angew. Chem. Int. Ed. 2007, 46, 912.
  (c) Kramer, S.; Odabachian, Y.; Overgaard, J.; Rottländer, M.; Gagosz, F.; Skrydstrup, T. Angew. Chem. Int. Ed. 2011, 50, 5090.
29. [29]
  (a) Li, H.; Zhang, W.-X.; Xi, Z. Chem. Eur. J. 2013, 19, 12859.
  (b) Xi, Z. F.; Li, P. X. Angew. Chem. Int. Ed. 2000, 39, 2950.
  (c) Xi, Z. F.; Song, Q. L.; Chen, J. L.; Guan, H. R.; Li, P. X. Angew. Chem. Int. Ed. 2001, 40, 1913.
30. [30]
  Cheng, X.; Zhu, L.; Lin, M.; Chen, J.; Huang, X. Chem. Commun. 2017, 53, 3745. doi: 10.1039/C7CC01368J
31. [31]
  Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612. doi: 10.1021/cr900074m
32. [32]
  (a) Xu, M.; Wang, Y.; Yang, F.; Wu, C.; Wang, Z.; Ye, B.; Jiang, X.; Zhao, Q.; Li, J.; Liu, Y.; Zhang, J.; Tian, G.; He, Y.; Shen, J.; Jiang, H. Eur. J. Med. Chem. 2018, 145, 74.
  (b) Ravi Ganesh, K.; Pachore, S. S.; Pratap, T. V.; Umesh, K.; Basaveswara Rao, M. V.; Murthy, C.; Suresh Babu, M. Synth. Commun. 2015, 45, 2676.
33. [33]
  (a) Shi, M.; Lu, J.-M.; Wei, Y.; Shao, L.-X. Acc. Chem. Res. 2012, 45, 641.
  (b) Zhang, D.-H.; Tang, X.-Y.; Shi, M. Acc. Chem. Res. 2014, 47, 913.
34. [34]
  Yamago, S.; Nakamura, E. Org. React. (Hoboken, NJ, U. S.), 2002, 61, 15.
35. [35]
  (a) Shen, X.-Y.; Peng, X.-S.; Wong, H. N. C. Org. Lett. 2016, 18, 1032.
  (b) Lu, X.-L.; Lyu, M.-Y.; Peng, X.-S.; Wong, H. N. C. Angew. Chem. Int. Ed. 2018, 57, 11365.
36. [36]
  Gibson, S. E.; Mainolfi, N. Angew. Chem. Int. Ed. 2005, 44, 3022. doi: 10.1002/anie.200462235
37. [37]
  Rios-Gutierrez, M.; Domingo, L. R. Eur. J. Org. Chem. 2019, 2019, 267. doi: 10.1002/ejoc.201800916
38. [38]
  Zhou, Y.-Y.; Uyeda, C. Science 2019, 363, 857. doi: 10.1126/science.aau0364
39. [39]
  (a) Binger, P.; Wedemann, P.; Kozhushkov, S. I.; de Meijere, A. Eur. J. Org. Chem. 1998, 1998, 113.
  (b) Binger, P.; Brinkmann, A.; Wedemann, P. Chem. Ber. Recl. 1983, 116, 2920.
  (c) Binger, P.; McMeekin, J. Angew. Chem. Int. Ed. 1974, 13, 466.
  (d) Binger, P.; McMeekin, J. Angew. Chem. Int. Ed. 1973, 12, 995.
  (e) Ohta, T.; Takaya, H.; Trost, B. M.; Fleming, I.; Paquette, L. A. Metal-catalyzed Cycloaddition of Small Ring Compounds, Petgamon, Oxford, 1991, p. 1185.
40. [40]
  Fu, N.-Y.; Chan, S.-H.; Wong, H. N. C. In The Chemistry of Cyclobutanes, 1 ed.; Eds.: Rappoport, Z., Liebman, J. F., John Wiley & Sons, Ltd., Chichester, 2005, p. 357.
41. [41]
  (a) Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. In Progress in Heterocyclic Chemistry, Vol. 21, Eds.: Gribble, G. W.; Joule, J. A., Elsevier, Oxford, UK, 2009, p. 179.
  (b) Hou X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry, Vol. 13, Eds.: Gribble, G. W.; Gilchrist, T. L., Elsevier, Oxford, UK, 2001, p. 130.
  (c) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955.
42. [42]
  Chen, F.; Chen, K.; Zhang, Y.; He, Y.; Wang, Y.-M.; Zhu, S. J. Am. Chem. Soc. 2017, 139, 13929. doi: 10.1021/jacs.7b08064
43. [43]
  (a) Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285.
  (b) Lanke, V.; Zhang, F.-G.; Kaushansky, A.; Marek, I. Chem. Sci. 2019, 10, 9548.
44. [44]
  O'Connor, A. R.; Urbin, S. A.; Moorhouse, R. A.; White, P. S.; Brookhart, M. Organometallics 2009, 28, 2372. doi: 10.1021/om801103p
45. [45]
  Minami, A.; Ozaki, T.; Liu, C.; Oikawa, H. Nat. Prod. Rep. 2018, 35, 1330. doi: 10.1039/C8NP00026C
46. [46]
  Yang, Y.-L.; Li, W.; Wang, H.; Yang, L.; Yuan, J.-Z.; Cai, C.-H.; Chen, H.-Q.; Dong, W.-H.; Ding, X.-P.; Jiang, B.; Mándi, A.; Kurtán, T.; Mei, W.-L.; Dai, H.-F. Fitoterapia 2019, 138.
47. [47]
  Krawczyk, A. R.; Jones, J. B. J. Org. Chem. 1989, 54, 1795. doi: 10.1021/jo00269a010
48. [48]
  (a) Lin, F.; Peng, H.-Y.; Chen, J.-X.; Chik, D. T. W.; Cai, Z.; Wong, K. M. C.; Yam, V. W. W.; Wong, H. N. C. J. Am. Chem. Soc. 2010, 132, 16383.
  (b) Wu, A.-H.; Hau, C.-K.; Wong, H. N. C. Adv. Synth. Catal. 2007, 349, 601.
  (c) Peng, H.-Y.; Lam, C.-K.; Mak, T. C. W.; Cai, Z.; Ma, W.-T.; Li, Y.-X.; Wong, H. N. C. J. Am. Chem. Soc. 2005, 127, 9603.
49. [49]
  Jackson, D. A.; Lacy, P. H.; Smith, D. C. C. J. Chem. Soc., Perkin Trans. 1 1989, 215.
50. [50]
  Gonzalez, M. J.; Gonzalez, J.; Vicente, R. Eur. J. Org. Chem. 2012, 2012, 6140. doi: 10.1002/ejoc.201201191
51. [51]
  (a) Meinwald, J.; Labana, S. S.; Chadha, M. S. J. Am. Chem. Soc. 1963, 85, 582.
  (b) House, H. O. J. Am. Chem. Soc. 1955, 77, 3070.
52. [52]
  Ma, D.; Miao, C.-B.; Sun, J. J. Am. Chem. Soc. 2019, 141, 13783. doi: 10.1021/jacs.9b07514
53. [53]
  Chang, M.-Y.; Lin, C.-H. J. Chin. Chem. Soc. (Taipei, Taiwan) 2011, 58, 853. doi: 10.1002/jccs.201190135
54. [54]
  Chang, M.-Y.; Lee, N.-C.; Lee, M.-F.; Huang, Y.-P.; Lin, C.-H. Tetrahedron Lett. 2010, 51, 5900. doi: 10.1016/j.tetlet.2010.08.090
55. [55]
  Duan, J. J. W.; Lu, Z.; Jiang, B.; Yang, B. V.; Doweyko, L. M.; Nirschl, D. S.; Haque, L. E.; Lin, S.; Brown, G.; Hynes, J.; Tokarski, J. S.; Sack, J. S.; Khan, J.; Lippy, J. S.; Zhang, R. F.; Pitt, S.; Shen, G.; Pitts, W. J.; Carter, P. H.; Barrish, J. C.; Nadler, S. G.; Salter-Cid, L. M.; McKinnon, M.; Fura, A.; Schieven, G. L.; Wrobleski, S. T. Biorg. Med. Chem. Lett. 2014, 24, 5721. doi: 10.1016/j.bmcl.2014.10.061
56. [56]
  Chang, M. Y.; Lee, N. C.; Lee, M. F.; Huang, Y. P.; Lin, C. H. Tetrahedron Lett. 2010, 51, 5900. doi: 10.1016/j.tetlet.2010.08.090
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